If I had that kind of time on that drive, I think I’d go out of my way to see Mammoth Cave in Kentucky.

Mapquest says the entire drive is 20+ hours, so that would give you time to stop and see the caves, and depending on the time you spent on the road the next day, you could stop at Gettysburg, PA before you get to New York.

Or you might prefer getting to NYC ASAP and doing the sights there: Circle Tour around Manhattan; Liberty Island to see the Statue of Liberty; Ellis Island; Rockefeller Center, etc.

If you are interested in architecture, a visit to Frank Lloyd Wright’s Fallingwater would be a wonderful stop to put on the list. Visiting there in the fall while the leave are changing is breath-taking.

I’d go to the Rock & Roll Hall of Fame near Cleveland. I’d also see some of the Alleghenies in Pennsylvania. It’s the ideal time of year for leaf peeping, if you’re into that sort of thing. Ooh, and I’d visit an Amish village, if possible, and get a mince pie.

You will probably hit western PA at the peak of the leaves changing. And O M G are you in for a treat. It is soooooooooooooooooooooooooooooooo beautiful. If you go anywhere near Pittsburgh and straight across the state, you’re gauranteed to see some good stuff. If you are a pizza fanatic I can also recommend the best pizza place in the world, which is in the Pittsburgh area. And you really should go. So PM me if you want that. :)

@RealEyesRealizeRealLies That would be fun, really, I’m serious, well at least I am now, now that you might actually consider it If you come during the day, we could go to Longwood Gardens. It’s a world class botanical garden and one of the things not to be missed near me. The greenhouses, at least, can be done in a couple of hours. When Rob Lindler visited we went there. You might have seen some of the photos on the kitkatkaosklub. :-). But if not, anytime is o.k. with me. And I’m a hell of a site less out of your way than Kentucky (!!!) and less out out of your way than Falling Water and Hershey, PA. I was also going to second @aprilsimnel on the Rock and Roll Hall of Fame and Museum in Cleveland. I was in Cleveland this past February visiting my Aunt and went to there just because I was there but the Rock and Roll Hall of Fame turned out to be much, much better than I actually thought it would be. I think it’s really worth the time.